Analysis of the intramolecular 1,7-lactone of N-acetylneuraminic acid using HPLC-MS: relationship between detection and stability.

IF 2.7 4区生物学 Q3 BIOCHEMISTRY & MOLECULAR BIOLOGY

Glycoconjugate Journal Pub Date : 2023-06-01 DOI:10.1007/s10719-023-10114-x

Paolo La Rocca, Ivana Lavota, Marco Piccoli, Federica Cirillo, Andrea Ghiroldi, Giuseppe Ciconte, Carlo Pappone, Pietro Allevi, Paola Rota, Luigi Anastasia

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Abstract

A subclass of the sialic acid family consists of intramolecular lactones that may function as key indicators of physiological and pathological states. However, the existence of these compounds in free form is highly improbable, since they are unlikely to exist in an aqueous solution due to their lability. Current analytical method used to detect them in biological fluids has not recognized their reactivity in solution and is prone to misidentification. However, recent advances in synthetic methods for 1,7-lactones have allowed the preparation of these sialic acid derivatives as authentic reference standards. We report here the development of a new HPLC-MS method for the simultaneous detection of the 1,7-lactone of N-acetylneuraminic acid, its γ-lactone derivative, and N-acetylneuraminic acid that overcomes the limitations of the previous analytical procedure for their identification.

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n -乙酰神经氨酸分子内1,7-内酯的HPLC-MS分析:检测与稳定性的关系。

唾液酸家族的一个亚类由分子内酯组成，可能作为生理和病理状态的关键指标。然而，这些化合物以自由形式存在是极不可能的，因为由于它们的不稳定性，它们不太可能存在于水溶液中。目前在生物流体中检测它们的分析方法还没有认识到它们在溶液中的反应性，容易出现误判。然而，近年来1,7-内酯合成方法的进展使得这些唾液酸衍生物的制备成为可靠的参考标准。本文报道了一种新的高效液相色谱-质谱同时检测n -乙酰神经氨酸及其γ-内酯衍生物的1,7-内酯和n -乙酰神经氨酸的方法，该方法克服了以往分析方法的局限性。

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来源期刊

Glycoconjugate Journal 生物-生化与分子生物学

CiteScore

6.00

自引率

3.30%

发文量

审稿时长

1 months

期刊介绍： Glycoconjugate Journal publishes articles and reviews on all areas concerned with: function, composition, structure, biosynthesis, degradation, interactions, recognition and chemo-enzymatic synthesis of glycoconjugates (glycoproteins, glycolipids, oligosaccharides, polysaccharides and proteoglycans), biochemistry, molecular biology, biotechnology, immunology and cell biology of glycoconjugates, aspects related to disease processes (immunological, inflammatory, arthritic infections, metabolic disorders, malignancy, neurological disorders), structural and functional glycomics, glycoimmunology, glycovaccines, organic synthesis of glycoconjugates and the development of methodologies if biologically relevant, glycosylation changes in disease if focused on either the discovery of a novel disease marker or the improved understanding of some basic pathological mechanism, articles on the effects of toxicological agents (alcohol, tobacco, narcotics, environmental agents) on glycosylation, and the use of glycotherapeutics. Glycoconjugate Journal is the official journal of the International Glycoconjugate Organization, which is responsible for organizing the biennial International Symposia on Glycoconjugates.